title: Collective synthesis of several 2,7'-cyclolignans and their correlation by chemical transformations.
abstract: Collective synthesis of anti-malarial 2,7'-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin (2) as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, 2 can be correlated with the neolignan (±)-kadangustin J (1) isolated from a different plant source, through a highly efficient dehydrative cyclization reaction with excellent diastereotopic differentiation of the veratryl group and concomitant construction of the C1–C7 bond. It is noteworthy that the first total synthesis of stereodivergent (±)-8,8'-epi-aristoligone (5), (±)-8'-epi-aristoligone (7), (±)-8'-epi-8-OH-aristoligone (8) and (±)-8'-epi-aristoligol (9) was demonstrated.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China. pengyu@lzu.edu.cn.
authors.forename: Yu
authors.initials: Y
authors.lastname: Peng
authors.forename: Zhen-Biao
authors.initials: ZB
authors.lastname: Luo
authors.forename: Jian-Jian
authors.initials: JJ
authors.lastname: Zhang
authors.forename: Long
authors.initials: L
authors.lastname: Luo
authors.forename: Ya-Wen
authors.initials: YW
authors.lastname: Wang
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000962:Antimalarials; D017705:Lignans; D013764:Tetrahydronaphthalenes